Emulsion



Patented July 11, 1933 PATENT OFFICE BENJAMIN R. HARRIS, OF CHICAGO, ILLINOIS EMULSION N Drawing.

My invention relates in general to im' proved emulsions, and more in particular to an improved margarine emulsion which Wlll not spatter during frying. The present application is a continuation in part of my prior application, Serial Number 475,623, filed August 15, 1930 as a division of application Serial No. 475,622, filed August 15, 1930, as a continuation in part of my prior application Serial No. 383,143, filed August- 2, 1929.

Those skilled in the art are referred to my co-pending application, Serial Number 566,156, filed September 30, 1931 a continuation in part of application Serial No. 475,622

In general the present invention represents J improve such forms of emulsion as margarine.

Another and very important ob]ect is to reduce the spattering of margarine when used for frying purposes and generally 1mprove its frying behavior.

Other objects and features of the invention will be apparent from a consideration of the following detailed description.

As was disclosed in my copending application, I have discovered a large class of chemical compounds which may be used to impart improved characteristics to all types of water-oil emulsions, particularly those used for cooking purposes, and other types of culinary fat preparations. These substances have several characteristics in common which make them very valuable in their use with margarine. These substances are compatible with mild acids and in particular with lactic acid in the concentration and under the conditions existing in margarine.

' In general they are diflicultly soluble in oils and fats and/or aqueous media and in many cases are substantiallyinsoluble. This makes it possible to use these compounds, in most Application filed September 30, 1931. Serial'No. 566,157.

cases in very small quantities, as they may be consldered to concentrate at the water-oil interface of the emulsion rather than be freely dissolved in either the water or oil phase. These substances are semi-colloidal or truly colloidal in character and are frequently colloidally disp'ersible in aqueous and/or oleaginous media. They are, moreover, substantially non-volatile at margarine frying temperatures and so will remain in the margarine and perform their function during frying.

One of the most important characteristics of these compounds is the presence in the molecule of two types of groups in balanced relation to each other, one group being hydrophyllic or water wetting in character, and the other group being lipophyllic or fat wetting in character. These groups must exist in the molecule in such a state ofbalance that they will'function at the water-oil interface in the intended manner. Presumably these substances orientate themselves at the interface, byreason of the balance of the two types of groups, but it is understood that the invention does not depend upon this explanation.

My prior application treats exhaustively of the manner in which the balance between the two groups may be determined so that without tests of any kind it is possible for the skilled colloid chemist-t0 pick out compounds which cannot function effectively as anti-spatterers,'as Well as'compounds which clearly will be effective as anti-spatterers.

However, there are compounds of 'such character that the state of balance existing between the two groups in the molecule is preferably determined by a simple quick test.

The balance of the hydrophile-lipophile groups in compounds which I employ in my invention is one of the characteristics and determinants of the class of substances which I employ. p v

A test which I have chosen as a means for determining the hydrophile-lipophile balance in organic c0m,p0unds, I call the spoon test. It is carried out as follows: From 0.05 to 0.20 gr. of the material or substance in .question is introduced into a porcelain mortar, wetted and ground into a smooth paste or solution with a pestle with a minimum proportion of water; two to five drops generally will suffice. 5 An ordinary margarine such for example as one made from vegetable oils, and fats, and cultured skimmed milk, and which possesses the usual property of spattering during frying is selected. Ten grams of this margarine are then introduced in small portions into the mortar and macerated thoroughly with the paste first prepared until the entire ten gram portion is thoroughly and uniformly intermixed with the material in the mortar. Two grams of this mixture are introduced into a tablespoon and held directly over a free flame such for example as a Bunsen flame, one or two inches long in such aposition that the point of the flame just about reaches the bottom of the spoon. A clean sheet of paper is placed on the bottom of the burner by inserting the stem of the Bunsen burner prior to lighting through a hole made in the center of the paper and allowing the paper to drop to the base of the burner .to catch the margarine splashed out during the heating. The mixture in the spoon is heated until all of the water is boiled off and the ebullition ceases and the spots on the paper observed.

If this treated margarine spots the paper to the same extent as the untreated margarine from which the former was prepared, then the lipophile and hydrophile groups of the compound are not balanced. The number and size of the spots on the paper or the added weight can be readily determined.

If the increase in weight of the paper or the number and character of the spots produced on the paper up until all the water has boiled off are less than that produced by simllarly heating two grams of the original untreated margarine employed for the test, then the material in question has balanced hydrophile-lipophile groups. The expression balanced lipophile and hydrophile groups used in the claims is to be interpreted in terms of the above described spoon tests,

and in the light of the entire disclosure, it being understood that in most cases the skilled chemist may select his compound without reference to the test.

My present invention has to do with a certain class of compounds of this general character, these new compounds all being characterized by the presence of hydroxy groups attached to carbon, and the 'hydrophyllic function being'exercised primarily by such hydroxy groups. These compounds contain at least one OX group linked to carbon, wherein 0 stands for oxygen, and X represents an edible cation.

Examples of some of the hydroxy substances which I have used as anti-spattering agents, many of them not known heretofore, and the preparation of many of which is described herein, are as follows:

Stearie acid ester of glucose Stearic acid esters of polyglycerols Stearyl sucrose Palmityl lactose Stearyl tartaric acid Stearyl citric acid (sodium salt) Digitonin Digitonin cholesteride Stearyl glycolic acid (sodium salt) Stearyl malic acid Pahnityl mucic acid Stearyl mannitol Glass A CHTCHFOH CH CHzCHzGHz-L OH Monopropionyl glucose Acetyl glycolic acid (sodium salt) Class B O C17Ha5-C-OH (Steane Acid) 0 CHx-(CH2)7OH(OH)(CHz)a-(4OH (Hydroxystearic Acid) Tetrapalmityl Glucose Cholesterol Palmityl Alcohol, CH (CH .,CH OH In the case of compoundsof both Class A" and Class B, anti-spattering powers are lacking because of inadequate balance between the lipophile and hydrophile groups. In the case of compounds of Class A, the hydrophile group dominates and is inadequately balanced by the lipophile group, that is, the lipophile characteristics of the latter are too weak to adequately balance and coact with the hydrophile group. In the case of substances of Class B, the reverse situation exists and anti-spattering power is absent because the lipophile grou is dominant and is inadequately balanced y the hydrophile group.

Glucosides and glucoside-like substances, such as some of. the saponins, in which the lipophyllic and hydrophyllic functions are qualitatively balanced, represent anti-spatterers in which the hydrophyllic function is dependent largely, if not entirely on OX groups. Digitonin is a case in point. As it is well known, digitonin yields four molecules of sugar on hydrolysis, as indicated herein below:

Digitonin is an efl'ective anti-spatterer in which, apparently the large accumulation of hydroxy groups, furnished particularly by the sugarresidues, supplies suflicient hydroph llic character to balance the digitogenin.

The saponin sterides, again, are anti-spatterers, in which hydroxyl groups play the principal, if not the entire hydrophyllic role. Digitonin cholesteride, prepare according to the method of Windaus (Hoppe-Zeylers Z. fur Phys. Chem. V. 65 (1910) pp. 110 to 117), is a good example of a saponin steride capable of acting as an anti-spatterer.

In general, I use relatively small proportions of the anti-spattering agents, up to 2% and in some instances as little as 1%, or less, but suflicient to effectively improve the frying behavior of the margarine; however, larger proportions may be used if desired.

I do not by any means restrict the use of these anti-spattering agents to margarine, inasmuch as they have many useful colloidal properties and can function as wetting, deterent, penetrating, emulsifying, frothing and oaming agents in the arts where such materials are employed. In fact, even in margarine, they function in other ways than merely to improve the frying characteristics.

One of these additional improvements is that the margarine is much less likel to leak and suffer from so-called weeping by virtue of the fact that the anti-spattering agent improves the emulsion in such a way that the water phase is much more tenaciously held in the margarine than otherwise.

A general method for the preparation of the anti-spattering agents with which the present application is concerned is to dissolve or suspend the hydroxy substance, freed of moisture, by drying or otherwise, in dry pyridine, with heating if necessary, cooling this mixture and introducing into it the requred amount of acyl chloride with agitation, either as such or dissolved in an inert solvent such as chloroform or carbon tetrachloride, care being taken throughout to exclude moisture as far as possible and to cool so as to control the heat of the reaction. The mixture is then allowed to stand at room temperature or is agitated at room temperature for six or ei' ht hours or longer and is then poured into iced dilute sulphuric acid or some other acidulating a t. The roduct enerally sefparates out, in the case 0 solid fatty acids, as a flocculent solid and in cases where acyl chlorides of liquid fatty acids have been used, generally speaking, as a liquid or semi-1i uid material. It may then be washed severa times with water or with brine at room tem rature or with the application of heat and finally separated from the water and dried.

A case in point is the method by which I prepare an anti-spattering ester of glucose. I prepare the Stearic acid ester of glucose as follows: Four parts of glucose (anhydrous) are dissolved in thirty parts of dry pyrldme, by warming. This solution is cooled and seven parts of stearyl chloride are added to it in small portions with simultaneous agitation and cooling. This mixture is allowed to stand at room temperatures for twenty-four hours and is then poured into iced dilute sulphuric acid. The solid material is washed several times with water and dried. This crude product which consists principally of monostearyl glucose, shows a relative anti-spattering power of approximately 90% when introduced into margarine 1n the proportion of one-half of one percent. In this procedure other basic materials such as dimethyl aniline, quinoline or quinaldine may be substituted for the pyridine. Also, the acylation may be carried out in a dlfi'erent medium or in an aqueous medium using a basic material such as calcium hydroxlde or carbonate to take care of the hydrochloric acid formed during the course of the reaction.

The products may be urified, if desired, by recrystallizing from so vents.

Some of the anti-spatterers of the class described herein which I prepared by the pfyridlne method are listed herein below, with t e pro ortions of the reacting materials used, in icated. The comparative anti-spattering powers of the fatty acid esters thus obtained are also shown. These anti-spat tering powers were determined by the method described in full in my co-pending application, above identified.

Comparative anti-spattering power of product Hydrophiie 8.5 pts. Hu- 8 crose. 6 pts. Tartaric acid. pts. Citric acid. 8pts.Lactoae 2 pts. Maiic 4 pts. Mani- 01. 4 pts. Mueie acid.

Acyl chloride Pyridine Btearyl chl ai 'i de. 10 pts. Stearyi chloos 'a Btearyl ride. 6.5 pts. Stearyl e. 8 ts. Paimityi oride.

Good.

Fair.

Moderate (sodium salt).

Good.

Good.

Very good.

Good.

the acy chloride I do not, of course, limit my invention to the products obtained by using the above listed reagents in the proportions indicated, nor do I even limit my invention to products obtained by the specific method above described, as the proportions and the reagents ma be varied. The scope of my invention inc udes compounds, however prepared, when such compounds comprise balanced lipophile and hydrophile groups and when their lipophile function is exercised by at least one-OX group.

Many other materials than those mentioned may be utilized to furnish the hydrophile function, for example, saccharic acid, gluconic acid, glucuronic acid, lactic acid, xylose, galactose, fructose, maltose, rhamnose, sorbitol, dulcitol, arabitol, and other hydroxy' substances with marked affinity for water.

Many other materials than those mentioned may be utilized assources of lipophile groups, for example, melissic acid, oleic acid, lauric acid, lauryl alcohol, palmityl alcohol, high molecular weight este s and other substances with marked affinity for oils and fats as pointed out more fully in my co-pending application. Serial No. 566,156.

I prepare the stearic acid esters of polyglycerols as follows: Fourteen hundred parts of anhydrous glycerol and thirty parts of fused sodium acetate are mixed and heated at 275 Centigrade for five hours With a stream of carbon dioxide gas bubbling through the mixture continuously. Nine hundred thirty parts of this reaction mixture are then treated with one hundred fifty-five parts of stearic acid and heated with continuous agitation for sixteen hours at 190 to 200 centigrade. The product is a tacky solid at room temperature. of a dark color, and emulsities readily with water. it can be introduced in this form into margarine without further purification. This product is a mixture of various stearic acid esters of polyglyeerols, which in part can be represented by mono-stearyl-tetraglycerol:

OH on The mixture is warmed to centigrade, and six parts oflinely powdered potassium permanganate are added with vigorous agitation over a period of about two hours. The manganese dioxide is then removed by treating with four parts of oxalic acid dissolved in titty parts of water containing five parts light petroleum naphtha. This extract is then neutralized with sodium carbonate.

The solvent is evaporated off, leaving behind so the sodium salt of stcaryl glycolic acid.

It must not be inferred from the preceding part of this specification that every antispattering substance of the character herein disclosed must be insoluble in oleaginous and/or aqueous media. It is true that the greater number of anti-spattering compounds of the present invention are substantially insoluble in these media, but there are a limited number of water soluble compounds which, if used in sufficiently larger proportions may have an effect in reducing spattering during frying.

It appears that in a given homologous series, there is a point or range at which lipophile and hydrophile characteristics are so balanced that an optimum power for the prevention of spattering is imparted to the molecule. Going from this point higher in the series in the direction of the increasing molecular weight in the lipophile group with a given hydrophile group, the anti-spattering power diminishes, because of excessive lipophile characteristics in the molecule; going down from this point or range lower in the series, anti-s 'iattering power again diminislics, because of the excessive hydrophile characteristics in the molecule; the tendency to dissolve in water concurrently increases. Tn certain homologous series, however, there are cases of water soluble substances which can function as anti-spattcrers. Examples This material possesses appreciable anti-spattering power.

of water soluble hydroxy compounds which may be used as anti-spatterers are 0 O l GHQ-CH CHCHrCHrCHrCHrdl-OCH-dl6ONa Octoyl malic acid (sodium salt) H2C-C'ONB Ill 0 i-di-QONa Octoy1tartaric acid (sodium salt) I HC-CONB Octoyl Dextrose Still another method of preparation is the procedure by which I make stearyl glycolic acid: Five parts of monostearine are dissolved in fifty parts of glacial acetic acid.

In general it is true, other things being equal, that a water soluble substance is not as effective as one that is not freely soluble in water.

It is also true that the total number of available anti-spatterers not soluble in water is greater than the number of soluble ones.

This is apparent from the following consideration. Generally, water solubility is negligible in anti-spatterers with a relatively large number of carbons in the lipophile group. As the number of carbons in the lipophile is decreased, however, toward the lower end of the series water solubility gradually increases, until finally the compounds become so prevailingly hydrophylliq that anti-spattering power is absent. In general, therefore, the total number of water soluble anti-spattering compounds is relatively small.

The compounds described above are of unusual importance in connection with their use with water-oil emulsions of all kinds, but they have a particular adaptation for use with all culinary emulsion products such as margarine. Commercial margarine after being treated with my anti-spatterin agent, when fried in a shallow pan exhi its improved frying behavior in that it allows its water to boil ofi' quietly, fries in a pleasing and comparatively quiet manner with the formationof considerable turbid froth and foam after the manner of butter, reduces the tendency of the curd to stick to the bottom of the frying pan, and reduces the amount of material which escapes from the pan by spattering. Untreated margarine on the other hand, when fried bumps turbulently, sputters noisily, and foams comparatively little. Also what little foam there is is trans arent and of an entirely different character rom that obtained from margarine previously treated with an antispatterer.

My emulsion improvers may be introduced into the margarine in a number of ways, as long as a satisfactory dispersion is obtained. For instance, the main constituents of margarine are edible oils and fats and cultured milk, and the anti-spattering or improving compounds may be introduced either into the oils or milk in any suitable manner. They may also be introduced into the churn during the production of the emulsion in its liquid state, care being taken to bring about the necessary dispersion. Or, the anti-spattering material may be used in a dry condition and mixed with the salt which is worked into the crystallized margarine, or the antispattering material may be made into a paste with milk, and kneaded in, or blended into the margarine.

As to the specific application of the invention to margarine and other emulsions or oleaginous culinary preparations, it is clear that since there are many hydroxy compounds containing balanced hydrophile and lipophile groups, it is impractical and unnecessary to list each particular combination of groups which can be used in accordance with my invention. Moreover, while I leave something to the skill of persons app-lying my invention, my description is who y sufliciently exhaustive, particularly when considered with respect to my prior applications, to enable those skilled in the art to successfully practice the same.

The term non-spattering margarine as used in the claims, is employed to desi ate a margarine, the frying behavior of which is improved by the addition thereto of the novel compounds of my invention herein described to reduce spattering. Margarine is used in the sense in which this term is employed in the U. S. revised statutes; in other words, it includes plastic emulsions of animal or vegetable fats, or mixtures thereof with sweet or ripened milk or water, either colored or uncolored. Edible emulsions of oleaginous materials and brine intended for human consumption are also included,or any like fatt aqueous composition which may be used 1n What I claim as new and desire to protect by Letters Patent of the United States is 1. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having included therein a proportion of an improver in the form of a non-nitrogenous chemical substance having balanced lipophile and hydrophile groups, the hydrophile function being exercised rimarily by at least one OX group linked to carbon, wherein 0 represents oxygen, and X stands for an innocuous cation.

2. An improved non-s attering margarine emulsion including an o eaginous phase, an aqueous phase, an having included therein a proportion of an improver in the form of a chemical substance characterized by a coaction in its molecule of balanced li ophile and hydrophile groups, the hydrophi e function beipig exercised primarily by at least one 0 group linked to a carbonyl carbon as m wherein C and 0 represent carbon and oxygen respectively, and X stands for an innocuous cation.

3. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having lncluded therein a proportion of an improver in the form of a non-nitrogenous ester characterized b a co-action in its molecule of balanced hy rophile and lipophile groups, the hydrophile function being exercised by at least one -OX group linked to carbon, wherein 0 stands for oxygen and X stands for an innocuous cation.

4. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having included therein group linked to a carbonyl carbon as in wherein C and 0 represent carbon and oxygen respectively, and X stands for an innocuous cation.

5. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having included therein a proportion of a non-nitrogenous ester of stearic acid capable of reducing spattering during frying, said ester of stearic acid having balanced hydrophile and lipophile groups, the hydrophile function being exercised by at least one -OX group linked to carbon wherein 0 represents oxygen and X stands for an innocuous cation.

6. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having included therein a proportion of an ester of stearic acid capable of reducing spattering during frying, said ester of stearic acid having balanced hydrophile and lipophile groups, the hydrophile function being exercised primarily by at least one'OX group linked to a carbonyl carbon as in wherein C and 0 represent carbon and oxygen respectively and X stands for innocuous cations.

7. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having included therein a proportion of a stearyl ester of a polyhydroxy substance characterized by a coaction in its molecule of balanced hydrophile and lipophile groups, the hydrophile function being exercised primarily by at least two OX groups linked to carbon, wherein O represents oxygen and X stands for innocuous cations.

8. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having included therein a proportion of a stearyl ester of a polyhydroxy substance characterized by a coaction in its molecule of balanced hydrophile and lipophile groups, the hydrophile function being exercised primarily by at least one OX group linked to a carbonyl carbon as in wherein C and 0 represent carbon and oxygen respectively and X stands for innocuous cations.

9. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having included therein a stearic acid ester of a sugar, the molecule as a whole having balanced hydrophile and lipophile groups.

10. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having included therein a proportion of a stearic acid ester of glucose said ester having balanced hydrophile and lipophile groups.

11. An improved non-spattering margarine emulsion including an oleaginous phase,

an aqueous phase, and having included therein a proportion of monostearyl glucose.

12. An improved non-spattering margarine emulsion includin an oleaginous phase, an aqueous phase, and approximately onehalf percent of monostearyl glucose.

13. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having included therein a proportion of a stearic acid ester of a water soluble carboxylic acid, the molecule as a whole having balanced lipophile and hydrophile groups.

14. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having included therein a proportion of stearyl malic acid.

15. An improved non-spattering margarine, including an oleaginous phase and an aqueous phase and an improving agent in the form of a non-nitro enous chemical substance having balanced llpophile and hydrophile groups, the hydrophile function being exercised primarily by at least one -OX group linked to carbon, wherein 0 represents oxygen and X stands for an innocuous cation, said substance being substantially insoluble in aqueous and oleaginous media, substantially nonvolatile at Water boiling temperature, and compatible with mild acids.

16. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having included therein a proportion of a non-nitrogenous water soluble substance having balanced lipophile and hydrophile groups, the hydrophile function being exercised primarily by at least one -()X group linked to carbon, wherein 0 represents oxygen, and X stands for an innocuous cation, the lipophile group having at least eight carbon atoms.

17. An improved non-spattering margarine emulsion including an oleaginous phase, an aqueous phase, and having included therein a proportion of an improver in the form of a water soluble substance characterized by a coaction in its molecule of balanced lipophile and hydrophile groups, the hydrophile function being exercised primarily by at least one OX group linked to a carbonyl carbon as m wherein C and 0 represent carbon and oxygen respectively, and X stands for an innocuous cation, the lipophile group having at least eight carbon atoms.

18. An improved non-sputtering margarine emulsion including an olcaginous phase, an aqueous phase, and having included therein a proportion of octoyl malic acid sodium salt.

19. An emulsion comprising an oleaginous phase, an aqueous phase, and having included therein a proportion of an emulsifying agent in the form of a non-nitrogenous chemical substance having balanced lipophile and hydrophile groups, the hydrophile function being exercised primarily by at least one OX group linked to carbon, wherein O represents oxygen, and X stands for an innocuous cation. and the lipophile function being exercised primarily by a fatty acid radical having at least eight carbon atoms.

20. An emulsion comprising an oleaginous phase, an aqueous phase, and having included therein a proportion of an emulsifying agent in the form of a non-nitrogenous chemical substance having balanced lipophile and hydrophile groups in 'the form of a chemical substance characterized by a coaction in its molecule of balanced lipophile and hydrophilc groups, the hydropbile function being exercised primarily by at least one -OX group linked to a carbonyl carbon as in ox, wherein C and 0 represent carbon and oxygen respectively, and X stands for an innocuous cation and the lipoh lc function being exercised primarily by a fatty acid radical having at least eight carbon atoms.

21.. An emulsion comprising an oloaginous phase, an aqueous phase, and having included therein a proportion of an emulsifying agent in the form of a non-nitrogenous chemical substance having balanced lipophile and hydrophile groups in the form of a non-nitrogenous ester characterized by a coaction in its molecule of balanced hydrophile and lipophilc groups, the hydrophile function being exereised by at least one --OX group linked to carbon, wherein 0 stands for oxygen. and X stands for an innocuous cation and the lipophile function being exercised primarily by a fatty acid radical having at least eight carbon atoms.

22. An emulsion comprising an. oleaginous phase, an aqueous phase, and having included therein a proportion of an emulsifying agentin the form of a non-nitrogenous chemical substance having balanced lipophile and by- (lroplnle groups in the form of an ester characterized by a coaction in its molecule of balanced hydropbile and lipophilo groups, the hydrophile unction being exercised rimarlly by at least one OX group link to a carbonyl carbon as in wherein G and 0 represent carbon and. oxygen respectively, and X stands for an innocuous cation and the li ophile function being exercised primaril by a fatty acid radical having at least eig t carbon atoms.

23. An emulsion comprising an oleaginous phase, an aqueous phase, and having included therein a proportion of an emulsifying agent in the form of a non'nitr enous chemical substance, having balanced llpophilc and bydrophile groups, said substance comprising stearyl ester of a polyhydroxy substance characterized by a coaction in its molecule of balanced hydrophile and lipophile groups, the hydrophile function being exercised primarily by at least two --OX groups linked to carbon, wherein 0 represents oxygen and X stands for an innocuous cation.

24. An emulsion comprising an oleaginous ph use, an aqueous phase, and having included therein a proportion of a stearyl ester of a polyhydroxy substance characterized by a reaction in its molecule of balanced hydro.- phile and lipophile groups, the hydrophile function being exercised primarily by at least one OX group linked to a carbonyl carbon as 1!! wherein C and 0 represent carbon and oxygen respectively and X stands for an innocuous cation.

25. An emulsion comprising an oleaginous phase and an aqueous phase, and having included therein a proportion of a chemical substance having balanced lipophile and hydrophile groups, wherein the lipophile group has at least four carbon atoms and wherein the hydrophile group is represented by the,

radical of a class of substance consisting of saccharic acid, gluconic acid, glucuronic acid, lactic acid, xylose, galactose, fructose, maltose, sorbitol, dulcitol, arabitol, sucrose, tartaric acid, citric acid, polyglycerols, lactose, malic acid and mucic acid.

26. An emulsion comprising an oleaginous phase and an aqueous phase, and having incl u :1 ed therein a proportion of a derivative of sucrose having balanced lipophile and hydrophile groups.

In witness whereof, I hereunto subscribe my name this 26th day of Sept., 1931.

' BENJAMIN R. HARRIS. 

